trilithium(1+) ion (3R)-3-hydroxy-2,2-dimethyl-3-({2-[(2-sulfanylethyl)carbamoyl]ethyl}carbamoyl)propyl ({[(2R,3R,5R)-5-(6-amino-9H-purin-9-yl)-3-(hydrogen phosphonatooxy)-4-hydroxyoxolan-2-yl]methyl phosphonato}oxy)phosphonate

• ChemBase ID: 164885
• Molecular Formular: C21H33Li3N7O16P3S
• Molecular Mass: 785.333303
• Monoisotopic Mass: 785.13974755
• SMILES: n1cnc2c(c1N)ncn2[C@H]1C([C@H]([C@H](O1)COP(=O)(OP(=O)([O-])OCC([C@H](C(=O)NCCC(=O)NCCS)O)(C)C)[O-])OP(=O)(O)[O-])O.[Li+].[Li+].[Li+]
• Canonical SMILES: SCCNC(=O)CCNC(=O)[C@@H](C(COP(=O)(OP(=O)(OC[C@H]1O[C@H](C([C@H]1OP(=O)(O)[O-])O)n1cnc2c1ncnc2N)[O-])[O-])(C)C)O.[Li+].[Li+].[Li+]
• InChI: InChI=1S/C21H36N7O16P3S.3Li/c1-21(2,16(31)19(32)24-4-3-12(29)23-5-6-48)8-41-47(38,39)44-46(36,37)40-7-11-15(43-45(33,34)35)14(30)20(42-11)28-10-27-13-17(22)25-9-26-18(13)28;;;/h9-11,14-16,20,30-31,48H,3-8H2,1-2H3,(H,23,29)(H,24,32)(H,36,37)(H,38,39)(H2,22,25,26)(H2,33,34,35);;;/q;3*+1/p-3/t11-,14?,15+,16+,20-;;;/m1.../s1
• InChIKey: QSCBPHBAFBVXRK-PBRODNJSSA-K

NAMES AND DATABASE IDS

Names

• IUPAC name: trilithium(1+) ion (3R)-3-hydroxy-2,2-dimethyl-3-({2-[(2-sulfanylethyl)carbamoyl]ethyl}carbamoyl)propyl ({[(2R,3R,5R)-5-(6-amino-9H-purin-9-yl)-3-(hydrogen phosphonatooxy)-4-hydroxyoxolan-2-yl]methyl phosphonato}oxy)phosphonate
• IUPAC Traditional name: trilithium(1+) ion (3R)-3-hydroxy-2,2-dimethyl-3-({2-[(2-sulfanylethyl)carbamoyl]ethyl}carbamoyl)propyl {[(2R,3R,5R)-5-(6-aminopurin-9-yl)-3-(hydrogen phosphonatooxy)-4-hydroxyoxolan-2-yl]methyl phosphonato}oxyphosphonate
• Synonyms: CoA Trilithium Salt; Trilithium Coenzyme A; Coenzyme A Trilithium Salt

Database IDs

• CAS Number: 18439-24-2
• PubChem SID: 162259019
• PubChem CID: 46907877

CALCULATED PROPERTIES

• Acid pKa: 0.8207411
• H Acceptors: 16
• H Donor: 7
• LogD (pH = 5.5): -10.367996
• LogD (pH = 7.4): -11.985149
• Log P: -5.765363
• Molar Refractivity: 159.3751 cm^3
• Polarizability: 64.550964 Å^3
• Polar Surface Area: 355.05 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C636400

A cofactor in enzymatic acetyl transfer reactions. It is the source of the phosphopantetheine group that is added as a prosthetic group to proteins such as acyl carrier protein and formyltetrahydrofolate dehydrogenase

REFERENCES

• Strickland K.C. et al.: J. Biol. Chem., 285, 1627 (2010)
• Elovson J. et al.: J. Biol. Chem., 243, 3603 (2010)